EP4204424A1 - Organic molecules for optoelectronic devices - Google Patents
Organic molecules for optoelectronic devicesInfo
- Publication number
- EP4204424A1 EP4204424A1 EP21773292.4A EP21773292A EP4204424A1 EP 4204424 A1 EP4204424 A1 EP 4204424A1 EP 21773292 A EP21773292 A EP 21773292A EP 4204424 A1 EP4204424 A1 EP 4204424A1
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- European Patent Office
- Prior art keywords
- optionally
- deuterium
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- group
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
- C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices.
- OLEDs organic light-emitting diodes
- the object of the present invention is to provide molecules which are suitable for use in optoelectronic devices. This object is achieved by the invention which provides a new class of organic molecules.
- Optoelectronic devices containing one or more light-emitting layers based on organics such as, e.g., organic light emitting diodes (OLEDs), light emitting electrochemical cells (LECs) and light-emitting transistors gain increasing importance.
- OLEDs are promising devices for electronic products such as screens, displays and illumination devices.
- optoelectronic devices based on organics are often rather flexible and producible in particularly thin layers.
- the OLED- based screens and displays already available today bear either good efficiencies and long lifetimes or good color purity and long lifetimes, but do not combine all three properties, i.e. good efficiency, long lifetime, and good color purity.
- optoelectronic devices which have a high quantum yield, a long lifetime, and good color purity.
- the color purity or color point of an OLED is typically provided by CIEx and CIEy coordinates, whereas the color gamut for the next display generation is provided by so-called BT-2020 and DCPI3 values.
- top emitting devices are needed to adjust the color coordinates by changing the cavity.
- a narrow emission spectrum in bottom emitting devices is required.
- the organic molecules according to the invention exhibit emission maxima in the deep blue, sky blue, green or yellow spectral range, preferably in the deep blue, sky blue, and green spectral range, and most preferably in the deep blue or green spectral range.
- the organic molecules exhibit in particular emission maxima between 420 and 580 nm, more preferably between 440 and 560 nm, even more preferably between 440 and 480 nm or between 500 and 550 nm, and most preferably between 440 and 465 nm or between 520 and 540 nm. Additionally, the molecules of the invention exhibit in particular a narrow - expressed by a small full width at half maximum (FWHM) - emission.
- the emission spectra of the organic molecules preferably show a full width at half maximum (FWHM) of less than or equal to 0.30 eV ( ⁇ 0.30 eV), unless stated otherwise, measured with 2% by weight of emitter in poly(methyl methacrylate) PMMA at room temperature (i.e.
- the photoluminescence quantum yields of the organic molecules according to the invention are 10% or more, preferably 30% or more, even more preferably 50% or more, and most preferably 60% or more.
- OLED organic light-emitting diode
- Corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable color and/or by employing the molecules according to the invention in an OLED display, a more accurate reproduction of visible colors in nature, i.e. a higher resolution in the displayed image, is achieved.
- the molecules can be used in combination with an energy pump to achieve hyper-fluorescence or hyper-phosphorescence.
- another species comprised in an optoelectronic device transfers energy to the organic molecules of the invention which then emit light.
- the organic molecules of the invention comprise or consist of a structure of formula I: Formula I wherein each of ring A, ring B, ring C, ring D, ring E, and ring F independently of each other represents an aromatic or heteroaromatic ring, each comprising 5 to 18 ring atoms, of which, in case of a heteroaromatic ring, 1 to 3 ring atoms are heteroatoms independently of each other selected from the group consisting of N, O, S, and Se.
- At least one ring of A, B, C, D, E, and F is a heteroaromatic ring.
- R 1 and R 3 are at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5-alkyl)3, Si(Ph)3, C 1 -C 5 -alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Ph, CN, CF 3 , or F; C 1 -C 5 -alkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkenyl, wherein optionally one or more
- R 1 is at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5-alkyl)3, Si(Ph)3, pyrrolidinyl, piperidinyl, C 1 -C 5 -alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Ph, CN, CF3, or F; C 1 -C 5 -alkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, or F; C1-C5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, or F; C2-C5-alkenyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, or F; C2-C5-alkynyl,
- R 1 is at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5-alkyl)3, Si(Ph)3, pyrrolidinyl, piperidinyl, C1-C5-alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Ph, CN, CF3, or F; C6-C18-aryl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , F, C 1 -C 5 -alkyl, SiMe 3 , SiPh 3 or C 6 -C 18 -aryl substituents; C 3 -C 17 -heteroaryl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , F, C 1 -C 5 -alkyl, SiM
- R 1 is at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, Me, benzyl, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, N(Ph)2, pyrrolidinyl, piperidinyl, Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu, CN, CF3, and Ph; carbazolyl, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu, CN, CF3, and Ph; wherein adjacent groups R 1 do not form an additional ring system; Y 1 and Y 2 are both NR 3 ; R 3 is at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, Me, i Pr, t Bu, C 6 -C 18 -aryl, wherein
- R 1 is at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, Me, benzyl, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, N(Ph)2, Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu, CN, CF3, and Ph; and carbazolyl, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu, CN, CF3, and Ph; wherein adjacent groups R 1 do not form an additional ring system; wherein Y 1 and Y 2 are both NR 3 ; wherein R 3 is at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, Me, benzyl, i Pr, t Bu, and Ph, which is optionally substituted with one or more substituents
- R 1 is at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, Me, benzyl, i Pr, t Bu, CN, CF3, N(Ph)2, Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu, CN, CF 3 , and Ph; and carbazolyl, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium and Ph; wherein adjacent groups R 1 do not form an additional ring system; wherein Y 1 and Y 2 are both NR 3 ; wherein R 3 is at each occurrence independently of each other selected from the group consisting of: hydrogen, deuterium, Me, benzyl, i Pr, t Bu, and Ph, which is optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu,
- more than one ring of A, B, C, D, E, and F is a heteroaromatic ring.
- exactly one ring of A, B, C, D, E, and F is a heteroaromatic ring.
- ring A is a heteroaromatic ring, while rings B, C, D, E, and F are aromatic rings that do not comprise a heteroatom in their core structure.
- ring B is a heteroaromatic ring, while rings A, C, D, E, and F are aromatic rings that do not comprise a heteroatom in their core structure.
- ring C is a heteroaromatic ring
- rings A, B, D, E, and F are aromatic rings that do not comprise a heteroatom in their core structure.
- ring D is a heteroaromatic ring
- rings A, B, C, E, and F are aromatic rings that do not comprise a heteroatom in their core structure.
- ring E is a heteroaromatic ring
- rings A, B, C, D, and F are aromatic rings that do not comprise a heteroatom in their core structure.
- ring F is a heteroaromatic ring
- rings A, B, C, D, and E are aromatic rings that do not comprise a heteroatom in their core structure.
- ring E is a five-membered heteroaromatic ring comprising exactly one heteroatom selected from O, S, and Se (in other words: E comprises or consists of a furan, thiophene or selenophene core), while rings A, B, C, D, and F in formula I are aromatic rings, each comprising up to 18 carbon atoms.
- ring F is a five-membered heteroaromatic ring comprising exactly one heteroatom selected from O, S, and Se (in other words: F comprises or consists of a furan, thiophene or selenophene core), while rings A, B, C, D, and E in formula I are aromatic rings, each comprising up to 18 carbon atoms.
- Y 1 and Y 2 are both oxygen (O).
- Y 1 and Y 2 are both sulfur (S).
- Y 1 and Y 2 are both selenium (Se).
- Y 1 and Y 2 are both NR 3 .
- the organic molecules comprise or consist of a structure of formula II or formula III:
- R I –R VIII and R 1 –R 48 are independently of each other selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5-alkyl)3, Si(Ph)3, pyrrolidinyl, piperidinyl, C1-C5-alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Ph, CN, CF3, or F; C1-C5-alkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, or F; C 1 -C 5 -thioalkoxy, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkenyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , or F
- R I and R II are independently of each other selected from the group consisting of: Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu, CN, or CF3;
- R III –R VIII and R 1 –R 48 are independently of each other selected from the group consisting of: hydrogen, deuterium, CF 3 , CN, F, Si(C 1 -C 5 -alkyl) 3 , Si(Ph) 3 , pyrrolidinyl, piperidinyl, C 1 -C 5 -alkyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Ph, CN, CF 3 , or F; C 6 -C 18 -aryl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 ,
- C 3 -C 17 -heteroaryl wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , F, C 1 -C 5 -alkyl, SiMe 3 , SiPh 3 or C 6 -C 18 -aryl substituents; N(C 6 -C 18 -aryl) 2 , N(C3-C17-heteroaryl)2; and N(C3-C17-heteroaryl)(C6-C18-aryl); wherein one or both pairs of adjacent substituents R 10 and R 11 as well as R 14 and R 15 in formula II optionally form an aromatic or heteroaromatic ring system, which is fused to the adjacent benzene ring b or c of formula II and optionally substituted with one or more substituents independently selected from: hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, and Ph, wherein optionally one or more hydrogen atoms are independently substitute
- R I and R II are independently of each other selected from the group consisting of: Me, i Pr, t Bu, CN, CF3, and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu, CN, or CF3;
- R III –R VIII and R 1 –R 48 are independently of each other selected from the group consisting of: hydrogen, deuterium, Me, benzyl, i Pr, t Bu, CF3, CN, F, SiMe3, Si(Ph)3, pyrrolidinyl, piperidinyl, C6-C18-aryl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, F, C1-C5-alkyl, SiMe3, SiPh3 or C6-C18-aryl substituents.
- carbazolyl wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF 3 , F, C 1 -C 5 -alkyl, SiMe 3 , SiPh 3 or C 6 -C 18 -aryl substituents; N(C 6 -C 18 -aryl) 2 , N(C 3 -C 17 -heteroaryl) 2 ; and N(C 3 -C 17 -heteroaryl)(C 6 -C 18 -aryl); wherein one or both pairs of adjacent substituents R 10 and R 11 as well as R 14 and R 15 in formula II optionally form an aromatic ring system, which is fused to the adjacent benzene ring b or c of formula II and optionally substituted with one or more substituents independently selected from: hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 , and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium
- R I and R II are independently of each other selected from the group consisting of: Me, i Pr, t Bu, CN, CF3, and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu, CN, or CF 3 ;
- R III –R VIII and R 1 –R 48 are independently of each other selected from the group consisting of: hydrogen, deuterium, Me, benzyl, i Pr, t Bu, CF3, CN, F, SiMe3, Si(Ph)3, N(Ph)2, pyrrolidinyl, piperidinyl, Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, Me, i Pr, t Bu or Ph substituents; carbazolyl, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, CN, CF3, Me, i Pr, t Bu, or
- R I and R II are independently of each other selected from the group consisting of: Me, i Pr, t Bu, and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu, and Ph;
- R III –R VIII and R 1 –R 48 are independently of each other selected from the group consisting of: hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, N(Ph)2, Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu or Ph substituents; wherein one or both pairs of adjacent substituents R 10 and R 11 as well as R 14 and R 15 in formula II optionally form an aromatic ring system, which is fused to the adjacent benzene ring b or c of formula II and optionally substituted with one or more substituents independently selected from: hydrogen, deuterium, Me, i Pr, t Bu,
- none of the pairs selected from R 3 and R 4 , R 8 and R 9 , R 16 and R 17 , R 21 and R 22 in formula II forms a group Z 1 ; and none of the pairs selected from R 27 and R 28 , R 32 and R 33 , R 40 and R 41 , R 45 and R 46 in formula III forms a group Z 2 .
- R 8 and R 9 as well as R 16 and R 17 in formula II form a group Z 1 , which is selected from selenium (Se) and NR X , with the provision that both Z 1 are identical.
- R 3 and R 4 as well as R 21 and R 22 in formula II form a group Z 1 , which is selected from selenium (Se) and NR X , with the provision that both Z 1 are identical.
- all of the pairs R 3 and R 4 , R 8 and R 9 , R 16 and R 17 as well as R 21 and R 22 in formula II form a group Z 1 , which is selected from selenium (Se) and NR X , with the provision that all four Z 1 are identical.
- R 32 and R 33 as well as R 40 and R 41 in formula III form a group Z 2 , which is selected from selenium (Se) and NR X , with the provision that both Z 2 are identical.
- R 27 and R 28 as well as R 45 and R 46 in formula II form a group Z 2 , which is selected from selenium (Se) and NR X , with the provision that both Z 2 are identical.
- all of the pairs R 27 and R 28 , R 32 and R 33 , R 40 and R 41 as well as R 45 and R 46 in formula II form a group Z 2 , which is selected from selenium (Se) and NR X , with the provision that all four Z 2 are identical.
- X 1 is oxygen (O).
- X 1 is sulfur (S).
- X 1 is selenium (Se).
- X 2 is oxygen (O).
- X 2 is sulfur (S).
- X 2 is selenium (Se).
- the organic molecules comprise or consist of a structure according to formula II, wherein the aforementioned definitions apply. In one embodiment of the invention, the organic molecules comprise or consist of a structure according to formula III, wherein the aforementioned definitions apply.
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h: It is understood that all definitions given within certain embodiments of the invention referring to formula II may also apply to formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, and II-h.
- formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h each represent a fraction of the scope of molecules represented by formula II so that not all parts of the abovementioned definitions related to formula II can apply to formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, and II-h.
- formula II-a excludes that one or more pair selected from R 3 and R 4 , R 8 and R 9 , R 16 and R 17 , R 21 and R 22 within formula II optionally form a group Z 1 .
- formulas III-a, III-b, III-c, III-d, III-e, III-f, III-g, III-h each represent a fraction of the scope of molecules represented by formula III so that not all parts of the abovementioned definitions related to formula III can apply to formulas III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h.
- formula III-a excludes that one or more pair selected from R 27 and R 28 , R 32 and R 33 , R 40 and R 41 , R 45 and R 46 within formula III optionally form a group Z 2 .
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein X 1 and X 2 are oxygen (O) and wherein apart from that the aforementioned definitions apply.
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein X 1 and X 2 are sulfur (S) and wherein apart from that the aforementioned definitions apply.
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein X 1 and X 2 are selenium (Se), and wherein apart from that the aforementioned definitions apply.
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein Z 1 and Z 2 are selected from selenium (Se) and NR X , with the provision that all groups Z 1 or Z 2 contained in a molecule according to the named formulas are identical, and wherein apart from that the aforementioned definitions apply.
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein Z 1 and Z 2 are at each occurrence selenium (Se), and wherein apart from that the aforementioned definitions apply.
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein Z 1 and Z 2 are at each occurrence NR X , and wherein apart from that the aforementioned definitions apply.
- the organic molecules comprise or consist of a structure according to any of formulas II-a, II-b, III-a, and III-b, wherein the aforementioned definitions apply.
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein X 1 and X 2 are selected from oxygen (O), sulfur (S), and selenium (Se);
- R I , R II , R V , R VI , R VII , and R VIII are independently of each other selected from the group consisting of: Me, i Pr, t Bu, CN, CF3, and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu, CN, or CF3;
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein X 1 and X 2 are selected from oxygen (O), sulfur (S), and selenium (Se);
- R I , R II , R V , R VI , R VII , and R VIII are independently of each other selected from the group consisting of: Me, i Pr, t Bu, and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu, and Ph;
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein X 1 and X 2 are selected from oxygen (O), sulfur (S), and selenium (Se);
- R I , R II , R V , R VI , R VII , and R VIII are independently of each other selected from the group consisting of: Me, i Pr, t Bu, and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu, and Ph;
- the organic molecules comprise or consists of a structure according to any of formulas II-a, II-b, II-c, II-d, II-e, II-f, II-g, II-h, III-a, III-b, III-c, III-d, III-e, III-f, III-g, and III-h, wherein X 1 and X 2 are selected from oxygen (O), sulfur (S), and selenium (Se);
- R I , R II , R V , R VI , R VII , and R VIII are independently of each other selected from the group consisting of: Me, i Pr, t Bu, and Ph, wherein optionally one or more hydrogen atoms are independently substituted by deuterium, Me, i Pr, t Bu, and Ph;
- cyclic group may be understood in the broadest sense as any mono-, bi- or polycyclic moieties.
- adjacent substituents R V and R VI , R VI and R VII as well as R VII and R VIII in formula III do not form an aromatic ring system which is fused to the adjacent benzene ring f ⁇ of formula III.
- ring and ring system may be understood in the broadest sense as any mono-, bi- or polycyclic moieties.
- ring atom refers to any atom which is part of the cyclic core of a ring or a ring structure, and not part of a substituent optionally attached to it.
- the term “carbocycle” may be understood in the broadest sense as any cyclic group in which the cyclic core structure comprises only carbon atoms that may of course be substituted with hydrogen or any other substituents defined in the specific embodiments of the invention. It is understood that the term “carbocyclic” as adjective refers to cyclic groups in which the cyclic core structure comprises only carbon atoms that may of course be substituted with hydrogen or any other substituents defined in the specific embodiments of the invention. As used throughout the present application, the term “heterocycle” may be understood in the broadest sense as any cyclic group in which the cyclic core structure comprises not just carbon atoms, but also at least one heteroatom.
- heterocyclic refers to cyclic groups in which the cyclic core structure comprises not just carbon atoms, but also at least one heteroatom.
- the heteroatoms may, unless stated otherwise in specific embodiments, at each occurrence be the same or different and be individually selected from the group consisting of N, O, S, and Se. All carbon atoms or heteroatoms comprised in a heterocycle in the context of the invention may of course be substituted with hydrogen or any other substituents defined in the specific embodiments of the invention.
- aromatic ring system may be understood in the broadest sense as any bi- or polycyclic aromatic moiety.
- heteromatic ring system may be understood in the broadest sense as any bi- or polycyclic heteroaromatic moiety.
- fused when referring to aromatic or heteroaromatic ring systems means that the aromatic or hetroaromatic rings that are “fused” share at least one bond that is part of both ring systems.
- naphthalene or naphthyl when referred to as substituent
- benzothiophene or benzothiphenyl when referred to as substituent
- fused aromatic ring systems in the context of the present invention, in which two benzene rings (for naphthalene) or a thiophene and a benzene (for benzothiophene) share one bond.
- sharing a bond in this context includes sharing the two atoms that build up the respective bond and that fused aromatic or heteroaromatic ring systems can be understood as one aromatic or heteroaromatic system.
- aryl and aromatic may be understood in the broadest sense as any mono-, bi- or polycyclic aromatic moieties.
- an aryl group contains 6 to 60 aromatic ring atoms
- a heteroaryl group contains 5 to 60 aromatic ring atoms, of which at least one is a heteroatom.
- the number of aromatic ring carbon atoms may be given as subscripted number in the definition of certain substituents.
- the heteroaromatic ring includes one to three heteroatoms.
- the terms “heteroaryl” and “heteroaromatic” may be understood in the broadest sense as any mono-, bi- or polycyclic hetero-aromatic moieties that include at least one heteroatom.
- heteroatoms may, unless stated otherwise in specific embodiments, at each occurrence be the same or different and be individually selected from the group consisting of N, O, S, and Se.
- arylene refers to a divalent substituent that bears two binding sites to other molecular structures and thereby serving as a linker structure.
- a group in the exemplary embodiments is defined differently from the definitions given here, for example, the number of aromatic ring atoms or number of heteroatoms differs from the given definition, the definition in the exemplary embodiments is to be applied.
- aryl group or “heteroaryl group” comprises groups which can be bound via any position of the aromatic or heteroaromatic group, derived from benzene, naphthaline, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, selenophene, benzoselenophene, isobenzos
- adjacent substituents bonded to an aromatic or heteroaromatic ring may together form an additional aliphatic or aromatic, carbocyclic or heterocyclic ring system which is fused to the aromatic or heteroaromatic ring to which the substituents are bonded. It is understood that the optionally so formed fused ring system will be larger (meaning it comprises more ring atoms) than the aromatic or heteroaromatic ring to which the adjacent substituents are bonded.
- the “total” amount of ring atoms comprised in the fused ring system is to be understood as the sum of ring atoms comprised in the aromatic or heteroaromatic ring to which the adjacent substituents are bonded and the ring atoms of the additional ring system formed by the adjacent substituents, wherein, however, the carbon atoms that are shared by the ring systems which are fused are counted once and not twice.
- a benzene ring may have two adjacent substituents that form another benzene ring so that a naphthalene core is built.
- This naphthalene core then comprises 10 ring atoms as two carbon atoms are shared by the two benzene rings and thus only counted once and not twice.
- adjacent substituents in this context refers to substituents attached to neighbouring ring atoms of a ring system.
- aliphatic when referring to ring systems may be understood in the broadest sense and means that none of the rings that build up the ring system is an aromatic or heteroaromatic ring.
- alkyl group may be understood in the broadest sense as any linear, branched, or cyclic alkyl substituent.
- alkyl comprises the substituents methyl (Me), ethyl (Et), n-propyl ( n Pr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i- butyl ( i Bu), s-butyl ( s Bu), t-butyl ( t Bu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2- pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl
- alkenyl comprises linear, branched, and cyclic alkenyl substituents.
- alkenyl group exemplarily comprises the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
- alkynyl comprises linear, branched, and cyclic alkynyl substituents.
- alkynyl group exemplarily comprises ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
- alkoxy comprises linear, branched, and cyclic alkoxy substituents.
- alkoxy group exemplarily comprises methoxy, ethoxy, n-propoxy, i- propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.
- thioalkoxy comprises linear, branched, and cyclic thioalkoxy substituents, in which the O of the exemplarily alkoxy groups is replaced by S.
- halogen and “halo” may be understood in the broadest sense as being preferably fluorine, chlorine, bromine or iodine. It is understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. naphthalene, dibenzofuran).
- the organic molecules according to the invention have an excited state lifetime of not more than 250 ⁇ s, of not more than 150 ⁇ s, in particular of not more than 100 ⁇ s, more preferably of not more than 80 ⁇ s or not more than 60 ⁇ s, even more preferably of not more than 40 ⁇ s in a film of poly(methyl methacrylate) (PMMA) with 2% by weight of organic molecule at room temperature (i.e. approximately 25 °C).
- PMMA poly(methyl methacrylate)
- the organic molecules according to the invention represent thermally-activated delayed fluorescence (TADF) emitters, which exhibit a ⁇ EST value, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1), of less than 5000 cm -1 , preferably less than 3000 cm 1 , more preferably less than 1500 cm 1 , even more preferably less than 1000 cm 1 or even less than 500 cm 1 .
- TADF thermally-activated delayed fluorescence
- the organic molecules according to the invention have an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 420 to 580 nm, with a full width at half maximum of less than 0.30 eV, preferably less than 0.28 eV, more preferably less than 0.25 eV, even more preferably less than 0.23 eV or even less than 0.20 eV in a film of poly(methyl methacrylate) (PMMA) with 2% by weight of organic molecule at room temperature (i.e. approximately 25 °C).
- Orbital and excited state energies can be determined either by means of experimental methods or by calculations employing quantum-chemical methods, in particular density functional theory calculations.
- the energy of the highest occupied molecular orbital E HOMO is determined by methods known to the person skilled in the art from cyclic voltammetry measurements with an accuracy of 0.1 eV.
- the energy of the lowest unoccupied molecular orbital E LUMO is determined as the onset of the absorption spectrum.
- the onset of an absorption spectrum is determined by computing the intersection of the tangent to the absorption spectrum with the x-axis.
- the tangent to the absorption spectrum is set at the low-energy side of the absorption band and at the point at half maximum of the maximum intensity of the absorption spectrum.
- the energy of the first excited triplet state T1 is determined from the onset the phosphorescence spectrum at 77K (steady-state spectrum; film of 2 % by weight of emitter in PMMA).
- the energy of the first excited singlet state S1 is determined from the onset the fluorescence spectrum at room temperature (i.e. approx. 25 °C; steady-state spectrum; film of 2 % by weight of emitter in PMMA).
- the onset of an emission spectrum is determined by computing the intersection of the tangent to the emission spectrum with the x-axis.
- the tangent to the emission spectrum is set at the high-energy side of the emission band and at the point at half maximum of the maximum intensity of the emission spectrum.
- the ⁇ EST value which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1), is determined based on the first excited singlet state energy and the first excited triplet state energy, which were determined as stated above.
- a further aspect of the invention relates to the use of an organic molecule according to the invention as a luminescent emitter or as an absorber, and/or as host material and/or as electron transport material, and/or as hole injection material, and/or as hole blocking material in an optoelectronic device.
- the optoelectronic device may be understood in the broadest sense as any device based on organic materials that is suitable for emitting light in the visible or nearest ultraviolet (UV) range, i.e., in the wavelength range from 380 nm to 800 nm. More preferably, the optoelectronic device may be able to emit light in the visible range, i.e., of from 400 nm to 800 nm.
- UV visible or nearest ultraviolet
- the optoelectronic device is more particularly selected from the group consisting of: • organic light-emitting diodes (OLEDs), • light-emitting electrochemical cells, • OLED sensors, in particular in gas and vapor sensors not hermetically shielded to the outside, • organic diodes, • organic solar cells, • organic transistors, • organic field-effect transistors, • organic lasers, and • down-conversion elements.
- OLEDs organic light-emitting diodes
- OLED sensors in particular in gas and vapor sensors not hermetically shielded to the outside
- organic diodes • organic solar cells
- organic transistors • organic field-effect transistors
- organic lasers • down-conversion elements.
- a light-emitting electrochemical cell comprises three layers, namely a cathode, an anode, and an active layer, which contains the organic molecule according to the invention.
- the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), an organic laser, and a light-emitting transistor.
- the light-emitting layer of an organic light-emitting diode comprises the organic molecules according to the invention.
- the light-emitting layer of an organic light-emitting diode comprises not only the organic molecules according to the invention but also a host material whose triplet (T1) and singlet (S1) energy levels are energetically higher than the triplet (T1) and singlet (S1) energy levels of the organic molecule.
- a further aspect of the invention relates to a composition
- a composition comprising or consisting of: (a) the organic molecule of the invention, in particular in the form of an emitter and/or a host, and (b) one or more emitter and/or host materials, which differ from the organic molecule of the invention, and (c) optionally, one or more dyes and/or one or more solvents.
- the composition has a photoluminescence quantum yield (PLQY) of more than 10 %, preferably more than 20 %, more preferably more than 40 %, even more preferably more than 60 % or even more than 70 % at room temperature.
- PLQY photoluminescence quantum yield
- compositions with at least one further emitter relates to a composition comprising or consisting of: (i) 0.5-50 % by weight, preferably 0.5-20 % by weight, in particular 0.5-10 % by weight, of the organic molecule according to the invention; (ii) 5-98 % by weight, preferably 30-93.9 % by weight, in particular 40-88% by weight, of one host compound H; (iii) 1-30 % by weight, in particular 1-20 % by weight, preferably 1-5 % by weight, of at least one further emitter molecule F with a structure differing from the structure of the molecules according to the invention; and (iv) optionally 0-93.5 % by weight, of one or more further host compound D with a structure differing from the structure of the molecules according to the invention; and (v) optionally 0-93.5 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent.
- the components or the compositions are chosen such that the sum of the weight of the components add up to 100 %.
- the composition has an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm.
- the at least one further emitter molecule F is a purely organic emitter.
- the at least one further emitter molecule F is a purely organic TADF emitter. Purely organic TADF emitters are known from the state of the art.
- the at least one further emitter molecule F is a fluorescence emitter, in particular a blue, a green, a yellow or a red fluorescence emitter.
- the composition, containing the at least one further emitter molecule F shows an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm, with a full width at half maximum of less than 0.30 eV, in particular less than 0.25 eV, preferably less than 0.22 eV, more preferably less than 0.19 eV or even less than 0.17 eV at room temperature, with a lower limit of 0.05 eV.
- the at least one further emitter molecule F is a green fluorescence emitter
- the at least one further emitter molecule F is a fluorescence emitter, in particular a green fluorescence emitter.
- the at least one further emitter molecule F is a fluorescence emitter selected from the following group:
- the composition has an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm, in particular between 485 nm and 590 nm, preferably between 505 nm and 565 nm, even more preferably between 515 nm and 545 nm.
- Composition wherein the at least one further emitter molecule F is a red fluorescence emitter In a further embodiment of the invention, the at least one further emitter molecule F is a fluorescence emitter, in particular a red fluorescence emitter. In one embodiment, the at least one further emitter molecule F is a fluorescence emitter selected from the following group:
- the composition has an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm, in particular between 590 nm and 690 nm, preferably between 610 nm and 665 nm, even more preferably between 620 nm and 640 nm.
- the light-emitting layer EML of an organic light-emitting diode of the invention comprises (or essentially consists of) a composition comprising or consisting of: (i) 0.5-50 % by weight, preferably 0.5-20 % by weight, in particular 0.5-10 % by weight, of one or more organic molecules according to the invention; (ii) 5-99 % by weight, preferably 30-94.9 % by weight, in particular 40-89% by weight, of at least one host compound H; and (iii) optionally 0-94 % by weight of or more further host compound D with a structure differing from the structure of the molecules according to the invention; and (iv) optionally 0-94 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent; and (v) optionally 0-30 % by weight, in particular 0-20 % by weight, preferably 0-5 % by weight, of at least one further emitter molecule
- energy can be transferred from the host compound H to the one or more organic molecules of the invention, in particular transferred from the first excited triplet state T1(H) of the host compound H to the first excited triplet state T1(E) of the one or more organic molecules according to the invention and/ or from the first excited singlet state S1(H) of the host compound H to the first excited singlet state S1(E) of the one or more organic molecules according to the invention.
- the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E HOMO (H) in the range of from -5 eV to -6.5 eV and one organic molecule according to the invention E has a highest occupied molecular orbital HOMO(E) having an energy E HOMO (E), wherein E HOMO (H) > E HOMO (E).
- the host compound H has a lowest unoccupied molecular orbital LUMO(H) having an energy E LUMO (H) and the one organic molecule according to the invention E has a lowest unoccupied molecular orbital LUMO(E) having an energy E LUMO (E), wherein E LUMO (H) > E LUMO (E).
- the light-emitting layer EML of an organic light-emitting diode of the invention comprises (or essentially consists of) a composition comprising or consisting of: (i) 0.5-50 % by weight, preferably 0.5-20 % by weight, in particular 0.5-10 % by weight, of one organic molecule according to the invention; (ii) 5-99 % by weight, preferably 30-94.9 % by weight, in particular 40-89% by weight, of one host compound H; and (iii) 0-94.5 % by weight of one or more further host compounds D with a structure differing from the structure of the molecules according to the invention; and (iv) optionally 0-94 % by weight, preferably 0-65 % by weight, in particular 0-50 % by weight, of a solvent; and (v) optionally 0-30 % by weight, in particular 0-20 % by weight, preferably 0-5 % by weight, of
- the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E HOMO (H) in the range of from -5 eV to -6.5 eV and the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy E HOMO (D), wherein E HOMO (H) > E HOMO (D).
- E HOMO (H) > E HOMO (D) favors an efficient hole transport.
- the host compound H has a lowest unoccupied molecular orbital LUMO(H) having an energy E LUMO (H) and the at least one further host compound D has a lowest unoccupied molecular orbital LUMO(D) having an energy E LUMO (D), wherein E LUMO (H) > E LUMO (D).
- E LUMO (H) > E LUMO (D) favors an efficient electron transport.
- the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E HOMO (H) and a lowest unoccupied molecular orbital LUMO(H) having an energy E LUMO (H)
- the at least one further host compound D has a highest occupied molecular orbital HOMO(D) having an energy E HOMO (D) and a lowest unoccupied molecular orbital LUMO(D) having an energy E LUMO (D)
- the organic molecule E of the invention has a highest occupied molecular orbital HOMO(E) having an energy E HOMO (E) and a lowest unoccupied molecular orbital LUMO(E) having an energy E LUMO (E), wherein E HOMO (H) > E HOMO (D) and the difference between the energy level of the highest occupied molecular orbital HOMO(E) of organic molecule according to the invention (E HOMO (H) > E HOMO (D) and the difference between
- Light-emitting layer EML comprising at least one further emitter molecule F
- the light-emitting layer EML comprises (or (essentially) consists of) a composition comprising or consisting of: (i) 0.5-50 % by weight, preferably 0.5-20 % by weight, in particular 0.5-10 % by weight, of one organic molecule according to the invention; (ii) 5-98 % by weight, preferably 30-93.9 % by weight, in particular 40-88% by weight, of one host compound H; (iii) 1-30 % by weight, in particular 1-20 % by weight, preferably 1-5 % by weight, of at least one further emitter molecule F with a structure differing from the structure of the molecules according to the invention; and (iv) optionally 0-93.5 % by weight, of one or more further host compound D with a structure differing from the structure of the molecules according to the invention; and (v) optionally 0-93.5 % by weight, preferably 0-65 % by weight, in particular
- the light-emitting layer EML comprises (or (essentially) consists of) a composition as described in Compositions with at least one further emitter, with the at least one further emitter molecule F as defined in Composition wherein the at least one further emitter molecule F is a green fluorescence emitter.
- the light-emitting layer EML comprises (or (essentially) consists of) a composition as described in Compositions with at least one further emitter, with the at least one further emitter molecule F as defined in Composition wherein the at least one further emitter molecule F is a red fluorescence emitter.
- energy can be transferred from the one or more organic molecules of the invention E to the at least one further emitter molecule F, in particular transferred from the first excited singlet state S1(E) of one or more organic molecules of the invention E to the first excited singlet state S1(F) of the at least one further emitter molecule F.
- the first excited singlet state S1(H) of one host compound H of the light- emitting layer is higher in energy than the first excited singlet state S1(E) of the one or more organic molecules of the invention E: S1(H) > S1(E), and the first excited singlet state S1(H) of one host compound H is higher in energy than the first excited singlet state S1(F) of the at least one emitter molecule F: S1(H) > S1(F).
- the first excited triplet state T1(H) of one host compound H is higher in energy than the first excited triplet state T1(E) of the one or more organic molecules of the invention E: T1(H) > T1(E), and the first excited triplet state T1(H) of one host compound H is higher in energy than the first excited triplet state T1(F) of the at least one emitter molecule F: T1(H) > T1(F).
- the first excited singlet state S1(E) of the one or more organic molecules of the invention E is higher in energy than the first excited singlet state S1(F) of the at least one emitter molecule F: S1(E) > S1(F).
- the first excited triplet state T1(E) of the one or more organic molecules E of the invention is higher in energy than the first excited singlet state T1(F) of the at least one emitter molecule F: T1(E) > T1(F). In one embodiment, the first excited triplet state T1(E) of the one or more organic molecules E of the invention is higher in energy than the first excited singlet state T1(F) of the at least one emitter molecule F: T1(E) > T1(F), wherein the absolute value of the energy difference between T1(E) and T1(F) is larger than 0.3 eV, preferably larger than 0.4 eV, or even larger than 0.5 eV.
- the host compound H has a highest occupied molecular orbital HOMO(H) having an energy E HOMO (H) and a lowest unoccupied molecular orbital LUMO(H) having an energy E LUMO (H)
- the one organic molecule according to the invention E has a highest occupied molecular orbital HOMO(E) having an energy E HOMO (E) and a lowest unoccupied molecular orbital LUMO(E) having an energy E LUMO (E)
- the at least one further emitter molecule F has a highest occupied molecular orbital HOMO(F) having an energy E HOMO (F) and a lowest unoccupied molecular orbital LUMO(E) having an energy E LUMO (F)
- Optoelectronic devices in a further aspect, relates to an optoelectronic device comprising an organic molecule or a composition as described herein, more particularly in the form of a device selected from the group consisting of organic light-emitting diode (OLED), light-emitting electrochemical cell, OLED sensor (particularly gas and vapor sensors not hermetically externally shielded), organic diode, organic solar cell, organic transistor, organic field-effect transistor, organic laser and down-conversion element.
- the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
- the organic molecule according to the invention is used as emission material in a light-emitting layer EML.
- the light-emitting layer EML consists of the composition according to the invention described herein.
- the optoelectronic device is an OLED, it may, for example, exhibit the following layer structure: 1. substrate 2. anode layer A 3. hole injection layer, HIL 4. hole transport layer, HTL 5. electron blocking layer, EBL 6. emitting layer, EML 7. hole blocking layer, HBL 8. electron transport layer, ETL 9. electron injection layer, EIL 10.
- the optoelectronic device may comprise one or more protective layers protecting the device from damaging exposure to harmful species in the environment including, exemplarily moisture, vapor and/or gases.
- the optoelectronic device is an OLED, which exhibits the following inverted layer structure: 1. substrate 2. cathode layer 3. electron injection layer, EIL 4. electron transport layer, ETL 5. hole blocking layer, HBL 6. emitting layer, B 7. electron blocking layer, EBL 8. hole transport layer, HTL 9. hole injection layer, HIL 10.
- the optoelectronic device is an OLED, which may exhibit stacked architecture. In this architecture, contrary to the typical arrangement, where the OLEDs are placed side by side, the individual units are stacked on top of each other. Blended light may be generated with OLEDs exhibiting a stacked architecture, in particular white light may be generated by stacking blue, green and red OLEDs.
- the OLED exhibiting a stacked architecture may comprise a charge generation layer (CGL), which is typically located between two OLED subunits and typically consists of a n-doped and p-doped layer with the n-doped layer of one CGL being typically located closer to the anode layer.
- the optoelectronic device is an OLED, which comprises two or more emission layers between anode and cathode.
- this so-called tandem OLED comprises three emission layers, wherein one emission layer emits red light, one emission layer emits green light and one emission layer emits blue light, and optionally may comprise further layers such as charge generation layers, blocking or transporting layers between the individual emission layers.
- the emission layers are adjacently stacked.
- the tandem OLED comprises a charge generation layer between each two emission layers.
- adjacent emission layers or emission layers separated by a charge generation layer may be merged.
- the substrate may be formed by any material or composition of materials. Most frequently, glass slides are used as substrates. Alternatively, thin metal layers (e.g., copper, gold, silver or aluminum films) or plastic films or slides may be used. This may allow a higher degree of flexibility.
- the anode layer A is mostly composed of materials allowing to obtain an (essentially) transparent film. As at least one of both electrodes should be (essentially) transparent in order to allow light emission from the OLED, either the anode layer A or the cathode layer C is transparent.
- the anode layer A comprises a large content or even consists of transparent conductive oxides (TCOs).
- TCOs transparent conductive oxides
- Such anode layer A may exemplarily comprise indium tin oxide, aluminum zinc oxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, wolfram oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or doped polythiophene.
- the anode layer A (essentially) consists of indium tin oxide (ITO) (e.g., (InO3)0.9(SnO2)0.1).
- the roughness of the anode layer A caused by the transparent conductive oxides (TCOs) may be compensated by using a hole injection layer (HIL). Further, the HIL may facilitate the injection of quasi charge carriers (i.e., holes) in that the transport of the quasi charge carriers from the TCO to the hole transport layer (HTL) is facilitated.
- the hole injection layer (HIL) may comprise poly-3,4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate (PSS), MoO2, V2O5, CuPC or CuI, in particular a mixture of PEDOT and PSS.
- the hole injection layer (HIL) may also prevent the diffusion of metals from the anode layer A into the hole transport layer (HTL).
- the HIL may exemplarily comprise PEDOT:PSS (poly-3,4- ethylendioxy thiophene: polystyrene sulfonate), PEDOT (poly-3,4-ethylendioxy thiophene), mMTDATA (4,4′,4′′-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2,2′,7,7′- tetrakis(n,n-diphenylamino)-9,9’-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1- phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB (N,N'-nis-(1-naphthalenyl)-N,N'-bis- phenyl-(1,1'-bipheny
- HTL hole transport layer
- any hole transport compound may be used.
- electron-rich heteroaromatic compounds such as triarylamines and/or carbazoles may be used as hole transport compound.
- the HTL may decrease the energy barrier between the anode layer A and the light-emitting layer EML.
- the hole transport layer (HTL) may also be an electron blocking layer (EBL).
- EBL electron blocking layer
- hole transport compounds bear comparably high energy levels of their triplet states T1.
- the hole transport layer may comprise a star- shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4- butylphenyl-diphenyl-amine)), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4′- cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA (4,4′,4′′-tris[2- naphthyl(phenyl)amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT- CN and/or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole).
- TCTA tris(4
- the HTL may comprise a p-doped layer, which may be composed of an inorganic or organic dopant in an organic hole-transporting matrix.
- Transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide may exemplarily be used as inorganic dopant.
- Tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes may exemplarily be used as organic dopant.
- the EBL may exemplarily comprise mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6- bis(triphenylsilyl)-9H-carbazole), and/or DCB (N,N′-dicarbazolyl-1,4-dimethylbenzene).
- Adjacent to the hole transport layer (HTL) typically, the light-emitting layer EML is located.
- the light-emitting layer EML comprises at least one light emitting molecule.
- the EML comprises at least one light emitting molecule according to the invention.
- the EML additionally comprises one or more host material.
- the host material is selected from CBP (4,4'-Bis-(N-carbazolyl)-biphenyl), mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2- yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2- (diphenylphosphino)phenyl] ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[[3-
- the host material typically should be selected to exhibit first triplet (T1) and first singlet (S1) energy levels, which are energetically higher than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.
- the EML comprises a so-called mixed-host system with at least one hole-dominant host and one electron-dominant host.
- the EML comprises exactly one light emitting molecule species according to the invention and a mixed-host system comprising T2T as electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]- 9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2- dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H- carbazole as hole-dominant host.
- a mixed-host system comprising T2T as electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenz
- the EML comprises 50-80 % by weight, preferably 60-75 % by weight of a host selected from CBP, mCP, mCBP, 9-[3- (dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3- (dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H- carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole; 10-45 % by weight, preferably 15-30 % by weight of T2T and 5-40 % by weight, preferably 10-30 % by weight of light emitting molecule according to the invention.
- a host selected from CBP, mCP, mCBP
- an electron transport layer Adjacent to the light-emitting layer EML an electron transport layer (ETL) may be located.
- ETL electron transport layer
- any electron transporter may be used.
- compounds poor of electrons such as, e.g., benzimidazoles, pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole), phosphinoxides and sulfone, may be used.
- An electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi).
- the ETL may comprise NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (Aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2 (2,7-di(2,2′-bipyridin-5-yl)triphenyle), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridin-3- yl)phenyl]benzene) and/or BTB (4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-bipheny
- the ETL may be doped with materials such as Liq.
- the electron transport layer (ETL) may also block holes or a holeblocking layer (HBL) is introduced.
- a cathode layer C may be located adjacent to the electron transport layer (ETL).
- the cathode layer C may comprise or may consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy.
- the cathode layer may also consist of (essentially) non-transparent metals such as Mg, Ca or Al.
- the cathode layer C may also comprise graphite and or carbon nanotubes (CNTs).
- the cathode layer C may also consist of nanoscalic silver wires.
- An OLED may further, optionally, comprise a protection layer between the electron transport layer (ETL) and the cathode layer C (which may be designated as electron injection layer (EIL)).
- This layer may comprise lithium fluoride, cesium fluoride, silver, Liq (8- hydroxyquinolinolatolithium), Li 2 O, BaF 2 , MgO and/or NaF.
- the electron transport layer (ETL) and/or a hole blocking layer (HBL) may comprise one or more host compounds.
- the light-emitting layer EML may further comprise one or more further emitter molecule F.
- Such an emitter molecule F may be any emitter molecule known in the art.
- an emitter molecule F is a molecule with a structure differing from the structure of the molecules according to the invention.
- the emitter molecule F may be a TADF emitter.
- the emitter molecule F may be a fluorescent and/or phosphorescent emitter molecule which is able to shift the emission spectrum and/or the absorption spectrum of the light-emitting layer EML.
- the triplet and/or singlet excitons may be transferred from the emitter molecule according to the invention to the emitter molecule F before relaxing to the ground state S0 by emitting light typically red-shifted in comparison to the light emitted by emitter molecule E.
- the emitter molecule F may also provoke two-photon effects (i.e., the absorption of two photons of half the energy of the absorption maximum).
- an optoelectronic device e.g., an OLED
- Exemplarily such white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and/or red light. Then, there may also optionally be energy transmittance between two or more molecules as described above.
- the designation of the colors of emitted and/or absorbed light is as follows: violet: wavelength range of >380-420 nm; deep blue: wavelength range of >420-480 nm; sky blue: wavelength range of >480-500 nm; green: wavelength range of >500-560 nm; yellow: wavelength range of >560-580 nm; orange: wavelength range of >580-620 nm; red: wavelength range of >620-800 nm.
- violet wavelength range of >380-420 nm
- deep blue wavelength range of >420-480 nm
- sky blue wavelength range of >480-500 nm
- green wavelength range of >500-560 nm
- yellow wavelength range of >560-580 nm
- orange wavelength range of >580-620 nm
- red wavelength range of >620-800 nm.
- emitter molecules such colors refer to the emission maximum.
- a deep blue emitter has an emission maximum in the range of from >420 to 480 nm
- a sky-blue emitter has an emission maximum in the range of from >480 to 500 nm
- a green emitter has an emission maximum in a range of from >500 to 560 nm
- a red emitter has an emission maximum in a range of from >620 to 800 nm.
- UHD Ultra High Definition
- a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20 or even more preferably between 0.08 and 0.18 or even between 0.10 and 0.15 and/ or a CIEy color coordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20 or even more preferably between 0.03 and 0.15 or even between 0.04 and 0.10.
- UHD Ultra High Definition
- a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.15 and 0.45 preferably between 0.15 and 0.35, more preferably between 0.15 and 0.30 or even more preferably between 0.15 and 0.25 or even between 0.15 and 0.20 and/ or a CIEy color coordinate of between 0.60 and 0.92, preferably between 0.65 and 0.90, more preferably between 0.70 and 0.88 or even more preferably between 0.75 and 0.86 or even between 0.79 and 0.84.
- UHD Ultra High Definition
- a further aspect of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.60 and 0.88, preferably between 0.61 and 0.83, more preferably between 0.63 and 0.78 or even more preferably between 0.66 and 0.76 or even between 0.68 and 0.73 and/ or a CIEy color coordinate of between 0.25 and 0.70, preferably between 0.26 and 0.55, more preferably between 0.27 and 0.45 or even more preferably between 0.28 and 0.40 or even between 0.29 and 0.35.
- a further aspect of the present invention relates to an OLED, which exhibits an external quantum efficiency at 14500 cd/m 2 of more than 10%, more preferably of more than 13%, more preferably of more than 15%, even more preferably of more than 17% or even more than 20% and/or exhibits an emission maximum between 500 and 560 nm, more preferably between 510 and 550 nm, even more preferably between 520 and 540 nm and/or exhibits an LT97 value at 14500 cd/m 2 of more than 100 h, preferably more than 250 h, more preferably more than 50 h, even more preferably more than 750 h or even more than 1000 h.
- a further aspect of the present invention relates to an OLED, which exhibits an external quantum efficiency at 1000 cd/m 2 of more than 8%, more preferably of more than 10%, more preferably of more than 13%, even more preferably of more than 15% or even more than 20% and/or exhibits an emission maximum between 420 and 500 nm, more preferably between 430 and 490 nm, even more preferably between 440 and 480 nm or still and/or exhibits an LT80 value at 500 cd/m2 of more than 100 h, preferably more than 200 h, more preferably more than 400 h, even more preferably more than 750 h or even more than 1000 h.
- the optoelectronic device in particular the OLED according to the present invention can be manufactured by any means of vapor deposition and/ or liquid processing. Accordingly, at least one layer is - prepared by means of a sublimation process, - prepared by means of an organic vapor phase deposition process, - prepared by means of a carrier gas sublimation process, - solution processed or - printed.
- the methods used to manufacture the optoelectronic device, in particular the OLED according to the present invention are known in the art.
- the different layers are individually and successively deposited on a suitable substrate by means of subsequent deposition processes. The individual layers may be deposited using the same or differing deposition methods.
- Vapor deposition processes exemplarily comprise thermal (co)evaporation, chemical vapor deposition and physical vapor deposition.
- an AMOLED backplane is used as substrate.
- the individual layer may be processed from solutions or dispersions employing adequate solvents.
- Solution deposition process exemplarily comprise spin coating, dip coating and jet printing.
- Liquid processing may be carried out in an inert atmosphere (e.g., in a nitrogen atmosphere) and the solvent may be completely or partially removed by means known in the state of the art.
- Procedures for synthesis scheme Ia Procedure 1 Under nitrogen atmosphere, an o-phenylenediamine derivative E1 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 , CAS 51364-51-3, 0.02 equiv.), tri-tert- butylphosphine (CAS 13716-12-6, 0.08 equiv.), and sodium tert-butoxide (CAS 865-48-5, 2.50 equiv.) are dissolved in dry toluene and heated to 100 °C.
- reaction mixture is stirred (approximately 15 h) at 140–180 °C and, upon cooling to room temperature, quenched by the addition of water. Extraction with dichloromethane and concentration under reduced pressure are followed by purification via MPLC or recrystallization to obtain the corresponding product M2 as a solid.
- the reaction mixture is stirred (approximately 15 h) at 140–180 °C and, upon cooling to room temperature, quenched by the addition of water. Extraction with dichloromethane and concentration under reduced pressure are followed by purification via MPLC or recrystallization to obtain the corresponding product M4 as a solid.
- the synthesis of the 3-chloro-N,N-diphenylaniline derivatives E2, E2-a, E2-b, E-5, E-5a, and E5-b can be achieved by means of classical Pd-catalyzed cross-coupling reactions (cf. the Buchwald Hartwig coupling), which are well-known to the person skilled in the art.
- Cyclic voltammetry Cyclic voltammograms are measured from solutions having concentration of 10 -3 mol/L of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g.0.1 mol/L of tetrabutylammonium hexafluorophosphate). The measurements are conducted at room temperature under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp2/FeCp2 + as internal standard. The HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).
- SCE saturated calomel electrode
- Density functional theory calculation Molecular structures are optimized employing the BP86 functional and the resolution of identity approach (RI). Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies are calculated with the B3LYP functional. Def2-SVP basis sets (and a m4-grid for numerical integration are used. The Turbomole program package is used for all calculations. Photophysical measurements Sample pretreatment: Spin-coating Apparatus: Spin150, SPS euro. The sample concentration is 0,2 mg/ml, dissolved in Toluene/DCM a suitable solvent. Program: 7- 30 sec. at 2000 U/min. After coating, the films are tried at 70 °C for 1 min.
- Photoluminescence Spectroscopy and Phosphorescence Spectroscopy For the analysis of Phosphorescence and Photoluminescence spectroscopy a fluorescence spectrometer "Fluoromax 4P" from Horiba is used. Time-resolved PL spectroscopy in the ⁇ s-range and ns-range (FS5) Time-resolved PL measurements were performed on a FS5 fluorescence spectrometer from Edinburgh Instruments. Compared to measurements on the HORIBA setup, better light gathering allows for an optimized signal to noise ratio, which favors the FS5 system especially for transient PL measurements of delayed fluorescence characteristics.
- the spectrometer comprises a 150W xenon arc lamp and specific wavelengths may be selected by a Czerny-Turner monochromator.
- the standard measurements were instead performed using an external VPLED variable pulsed LED with an emission wavelength of 310 nm.
- the sample emission is directed towards a sensitive R928P photomultiplier tube (PMT), allowing the detection of single photons with a peak quantum efficiency of up to 25 % in the spectral range between 200 nm to 870 nm.
- the detector is a temperature stabilized PMT, providing dark counts below 300 cps (counts per second).
- a tail fit using three exponential functions is applied.
- Photoluminescence quantum yield measurements For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0. Emission maxima are given in nm, quantum yields ⁇ in % and CIE coordinates as x,y values.
- PLQY is determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference 2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength 3) Measurement Quantum yields are measured for sample of films (2 % by weight of the emitter in PMMA) under nitrogen atmosphere. The yield is calculated using the equation: , wherein n photon denotes the photon count and Int. the intensity. Production and characterization of optoelectronic devices
- Optoelectronic devices, such as OLED devices, comprising organic molecules according to the invention can be produced via vacuum-deposition methods. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %.
- the total weight-percentage values amount to 100 %, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100 %.
- the (not fully optimized) OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current.
- the OLED device lifetime is extracted from the change of the luminance during operation at constant current density.
- the LT50 value corresponds to the time, where the measured luminance decreased to 50 % of the initial luminance
- analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80 % of the initial luminance, LT 95 to the time point, at which the measured luminance decreased to 95 % of the initial luminance etc.
- Accelerated lifetime measurements are performed (e.g. applying increased current densities).
- Exemplarily LT80 values at 500 cd/m 2 are determined using the following equation: wherein L 0 denotes the initial luminance at the applied current density. The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.
- HPLC-MS This analysis is performed on an HPLC-MS by Agilent (HPLC1260 Infinity) with MS-detector (Single Quadrupole).
- a typical HPLC method is as follows: a reverse phase column 3.0 mm x 100 mm, particle size 2.7 ⁇ m from Agilent (Poroshell 120EC-C18, 3.0 x 100 mm, 2.7 ⁇ m HPLC column) is used in the HPLC.
- HPLC-MS measurements are performed at 45 °C and a typical gradient is as follows: and the following solvent mixtures (all solvents contain 0.1% (V/V) of formic acid): An injection volume of 2 ⁇ L of a solution with a concentration of 0.5 mg/mL of the analyte is used for the measurements. Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source either in positive (APCI +) or negative (APCI -) ionization mode or an atmospheric pressure photoionization (APPI) source.
- APCI atmospheric pressure chemical ionization
- APCI + positive
- APCI - atmospheric pressure photoionization
- APPI atmospheric pressure photoionization
- Example 1 was synthesized according to the general procedure for synthesis (according to synthesis scheme Ia), wherein o-phenylenediamine, 5-chloro-N 1 ,N 1 ,N 3 ,N 3 -tetraphenyl- benzene-1,3-diamine, and 3,4-dibromo-2,5-diphenylselenophene were used as reactants E1, E2, and E3, respectively.
- Example 2 Example 1 was synthesized according to the general procedure for synthesis (according to synthesis scheme IIa), wherein o-phenylenediamine, 5-chloro-N 1 ,N 1 ,N 3 ,N 3 -tetraphenyl- benzene-1,3-diamine, and 3,4-dibromoselenophene were used as reactants E4, E5, and E6, respectively.
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